Windsor County Vacation Packages
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Your Windsor County Vacation
With a Windsor County vacation package, you can forget about planning hassles and instead focus on experiencing everything this exciting destination has on offer. Begin your trip to Windsor County with some time exploring Ludlow visiting popular sights like Weston Playhouse and Lake Rescue. Norwich is another top city that lures crowds from near and far. Quechee Gorge Bridge and Quechee Gorge Village are two of the leading places to see in this destination. From the instant you book your Windsor County vacation to the second you come back home, Expedia will take care of you each step of the way.
Top vacation destinations in Windsor County
Top Windsor County Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Landgrove
CA $1,310
per person
Nov 25 - Nov 30
found 15 hours ago
Roundtrip flight included
Toronto (YTO) to Rutland (RUT)
8.6/10 Excellent! (7 reviews)
We had a wonderful stay at The Landgrove! The owners were incredibly kind, welcoming, and helpful, making us feel right at home. It's a truly family-friendly place with a warm, personal touch that makes all the difference. The interiors are beautiful, cozy, and full of character, the food is delicious, and the fireplace in our room was absolutely amazing! Such a charming and special place. We would love to come back!
Reviewed on Oct 18, 2026
Okemo Mountain Lodging by Vail Resorts
Clock Tower Base Area
CA $2,213
per person
Nov 25 - Nov 30
found 15 hours ago
Roundtrip flight included
Toronto (YTO) to Springfield (VSF)
7.8/10 Good! (28 reviews)
Don’t ever rent at this place for the condo rentals they sent us to the wrong address, I could not get in contact with the so-called property manager for over an hour or more. We had no toilet paper, we had no hairdryer, no paper towels, we didn’t even know where the keys were or shampoo or soap. Basically this was an utter disaster. I tried to work it out with resort management and they offered certain things and I countered and I got at that point what I wanted, but it just continued to spiral downhill and then when I communicate further issues, I had to be on the phone with them, trying to explain to them what the problem was up until 11 PM at night, that night was in the 30s and they left the air conditioner on in the house didn’t warm up until after 1 AM. This was by far the worst experience I’ve ever had with a supposedly high-end resort. I’m telling you do not rent from their condo selection. It’s terrible. It’s expensive and it is just a waste of time.
Reviewed on Oct 15, 2026
Windsor County Hotel Deals
Woodstock Inn & Resort
Fourteen The Green Woodstock VT
CA $521
CA $635 total
Nov 16 - Nov 17
includes taxes & fees
Align Inn Vermont
5817 Woodstock Rd Quechee VT
CA $159
CA $174 total
Nov 5 - Nov 6
includes taxes & fees
9.4/10 Exceptional! (1,408 reviews)
"Very clean. Staff was very helpful. Close to restaurants and sites."
Reviewed on Oct 20, 2026
Jackson Gore Village, A Vail Resorts Property
111 Jackson Gore Road Ludlow VT
Fully refundableReserve now, pay when you stay
CA $260
CA $316 total
Nov 18 - Nov 19
includes taxes & fees
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Frequently asked questions
How much does a Windsor County vacation package cost?
Choose from any combination of hotels, flights and car rentals, and you can be vacationing in Windsor County from just CA $1,310. And the more you bundle, the more cash you save. The vacation of your dreams has never been more affordable.
How do I get a cheap travel package to Windsor County?
You'll save a ton of money if you bundle your hotels, car rentals and flights into a Windsor County travel package. Sometimes cheap packages mean fewer choices. But not with Expedia. We offer over 550 airlines and 1,000,000 hotels all over the world, which means you'll always have plenty of variety to choose from. Want to save even more? Add some exciting activities to your package deal to unlock even more bargains! After all, travel is about more than simply getting to your destination.
Where should I stay in Windsor County?
Okemo Mountain Resort is one of the key things that lures people to Windsor County, so it makes perfect sense that many decide to book their hotel in Ludlow.
What are the top hotels in Windsor County?
When it comes to hotels in Ludlow, Super 8 by Wyndham White River Junction and Holiday Inn Express Hotel & Suites White River Junction, an IHG Hotel are two terrific options. If you're spending time in Plymouth, Hotel Coolidge and White River Inn and Suites will make you feel right at home.
How far in advance should I book my Windsor County vacation?
It depends on the airline, but you can usually browse through international fares on Expedia up to a year in advance. While it's advisable to book ahead of time, lucky customers will sometimes find a cheaper flight only weeks before their intended journey.
What does an Expedia Windsor County travel package include?
It comes down to what you're looking for. If you're traveling by yourself, you might decide to bundle hotels and flights. Bringing the entire family to Windsor County? A travel package that includes hotels, rental cars and flights might suit you better. Expedia gives you the freedom and flexibility to tailor your travel package.
What should I know before booking a Windsor County travel package?
You'll save big with an Expedia travel package. Combine your flights, rental cars and hotels and be rewarded with great discounts. Hotels aren't your only choice, however. Book with us and take your pick of beachside condos, chalets in the middle of mountains and even glamping tents!
Can I choose my airline with a Windsor County Expedia vacation package?
Most definitely. Expedia has more than 550 partner airlines to select from across the world. With so many choices, finding the ideal carrier to fly you to Windsor County will be a snap.
If I'm not able to travel, can I cancel my Windsor County vacation package?
We get it — unexpected stuff happens. If you've locked in a Windsor County vacation package and need to amend or cancel it, we can help. It's always worth browsing our Customer Service Portal first for information. But generally, if you've booked your package within 24 hours, you may be able to amend or cancel your itinerary free of charge. If it's been more than 24 hours, your hotel, airline or car rental company may impose a charge.
Stay near popular Windsor County attractions
Okemo Mountain Resort
9.2/10 (510 reviews)
Hit the slopes in Ludlow with a visit to Okemo Mountain Resort. Discover the mountain views in this romantic area.
Photo by Mike Gauthier
Quechee Gorge Bridge
9.2/10 (580 reviews)
Quechee Gorge Bridge is just one of the places to see in White River Junction, so why not enjoy the other things to explore during your travels? Wander the riverfront in this quaint area.
Photo by George Sykes
King Arthur Baking Company
9.4/10 (178 reviews)
You can enjoy retail therapy at King Arthur Baking Company during your stay in Norwich. While you're in the area, stroll along the riverfront.
Photo by Ed Gaffny
Quechee Gorge Village
9.0/10 (288 reviews)
You can enjoy retail therapy at Quechee Gorge Village during your trip to Quechee. Amble around the area's riverfront or seek out the ski slopes.
Photo by William E Berry Jr.
Mount Ascutney
8.8/10 (27 reviews)
Commune with nature and explore the great outdoors at Mount Ascutney during your travels in Brownsville. You can seek out the ski slopes while in the area.
Billings Farm and Museum
9.2/10 (84 reviews)
You can study the exhibits at Billings Farm and Museum, a museum with a storied past, during your trip to Woodstock. Wander the riverfront in this quaint area.
Simon Pearce Mill
9.0/10 (80 reviews)
Learn about the local history of Quechee when you spend time at Simon Pearce Mill. Amble around this family-friendly area's riverfront and enjoy its top-notch restaurants.
Upper Valley Aquatic Center
8.0/10 (43 reviews)
Enjoy a stop at Upper Valley Aquatic Center, an entertaining place to visit in White River Junction. Wander the riverfront in this quaint area.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
